dimethyl (R,R)-(-)-trans-1,2-cyclohex-4-ene-1,2-dicarboxylate

Base Information

• Chemical Name: dimethyl (R,R)-(-)-trans-1,2-cyclohex-4-ene-1,2-dicarboxylate
• CAS No.: 150024-72-9
• Molecular Formula: C₁₀H₁₄O₄
• Molecular Weight: 198.219
• Mol file: 150024-72-9.mol

Synonyms:dimethyl (R,R)-(-)-trans-1,2-cyclohex-4-ene-1,2-dicarboxylate

Chemical Property of dimethyl (R,R)-(-)-trans-1,2-cyclohex-4-ene-1,2-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl (R,R)-(-)-trans-1,2-cyclohex-4-ene-1,2-dicarboxylate

There total 8 articles about dimethyl (R,R)-(-)-trans-1,2-cyclohex-4-ene-1,2-dicarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) + 1,4-dimethyl but-2-enedioate (23055-10-9) → (1S,2S)-cyclohex-4-ene-1,2-dicarboxylic acid dimethyl ester (137492-80-9) + dimethyl (R,R)-(-)-trans-1,2-cyclohex-4-ene-1,2-dicarboxylate (150024-72-9)

Guidance literature:

With C₁₆H₁₆Cl₂O₄Ti; In diethyl ether; dichloromethane; at -10 ℃; for 4h; Overall yield = 78 %; enantioselective reaction; Inert atmosphere;

DOI:10.13005/ojc/320217

Reference yield:

buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) + dimethylfumarate (624-49-7) → (1S,2S)-cyclohex-4-ene-1,2-dicarboxylic acid dimethyl ester (137492-80-9) + dimethyl (R,R)-(-)-trans-1,2-cyclohex-4-ene-1,2-dicarboxylate (150024-72-9)

Guidance literature:

With chiral titanium Lewis acid; In diethyl ether; hexane; dichloromethane; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1021/jo00027a074

Reference yield:

dimethyl trans-cyclohex-4-ene-1,2-dicarboxylate (17673-68-6) → dimethyl (R,R)-(-)-trans-1,2-cyclohex-4-ene-1,2-dicarboxylate (150024-72-9)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. KOH / ethanol

2: diethyl ether

With potassium hydroxide; In diethyl ether; ethanol;

DOI:10.1016/0040-4020(63)85050-4

upstream raw materials:

diazomethane

(1S,2S)-(+)-trans-cyclohex-4-ene-1,2-dicarboxylic acid

buta-1,3-diene

dimethylfumarate

Downstream raw materials:

(1S,2S)-(+)-trans-cyclohex-4-ene-1,2-dicarboxylic acid

(1R,2R)-α,α,α',α'-tetraphenylcyclohexane-1,2-dimethanol

(1R,2R)-1,2-cyclohexanedicarboxylic acid dimethyl ester

((1R,6R)-6-(hydroxymethyl)cyclohex-3-enyl)methanol

Refernces

• 1、 Choughule, Yogesh K.,Patwardhan, Anand V.. "Enantioselective Diels-Alder Reactions of Carboxylic Ester Dienophiles Catalysed by Titanium-Based Chiral Lewis Acid". . p. 921 - 926. Retrieved 2016/07/06.
• 2、 Ito, Yoshio N.,Ariza, Xavier,Beck, Albert K.,Bohac, Andrej,Ganter, Camille,et al.. "Preparation and Structural Analysis of Several New α,α,α',α'-Tetraaryl-1,3-dioxolane-4,5-dimethanols (TADDOL's) and TADDOL Analogs, Their Evaluation as Titanium Ligands in the Enantioselective Addition of Methyltitanium and Diethylzinc Reagents to Benzaldehyde, and Refinement of ...". . p. 2071 - 2110. Retrieved 2007/10/02.